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Identification
NameChlorpromazine
Accession NumberDB00477  (APRD00482)
TypeSmall Molecule
GroupsApproved
Description

The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class, chlorpromazine’s antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking dopamine receptors. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup. [PubChem]

Structure
Thumb
Synonyms
3-(2-chloro-10H-Phenothiazin-10-yl)-N,N-dimethyl-1-propanamine
3-(2-Chlorophenothiazin-10-yl)-N,N-dimethyl-propan-1-amine
Aminazine
Chlorderazin
Chloropromazine
Chlorpromados
Chlorpromazine
Chlorpromazinum
Clorpromazina
Contomin
CPZ
Largactil
N-(3-Dimethylaminopropyl)-3-chlorophenothiazine
Thorazine
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Chlorprom Tab 100mgtablet111.6 mgoralIcn Canada Ltd.1962-12-311998-08-13Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Chlorprom Tab 25mgtablet27.9 mgoralIcn Canada Ltd.1974-12-311998-08-13Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Chlorprom Tab 50mgtablet55.8 mgoralIcn Canada Ltd.1962-12-311998-08-13Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Chlorpromanyl 20 Syrdrops22.2 mgoralTechnilab Pharma Inc.1983-12-312004-08-03Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Chlorpromanyl 40 Drops Syr 44.5mg/mlsyrup44.5 mgoralTechnilab Pharma Inc.1986-12-312006-07-28Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Chlorpromazine HCl Inj 25mg/ml USPliquid25 mgintramuscular; intravenousMylan Pharmaceuticals Ulc1994-12-312015-11-03Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Chlorpromazine HCl Inj 27.9mg/mlliquid27.9 mgintramuscular; intravenousDavid Bull Laboratories (Pty) Ltd.1985-12-311996-09-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Chlorpromazine HCl Inj USPsolution25 mgintramuscular; intravenousAlveda Pharmaceuticals IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Chlorpromazine Hydrochloride Injectionliquid27.9 mgintramuscular; intravenousSandoz Canada Incorporated1988-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Chlorpromazine Tab 25mgtablet27.9 mgoralDuchesnay Inc1978-12-312003-07-18Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Chlorpromazine Tablets B.P. 100mgtablet100 mgoralClonmel Healthcare Limited1992-12-311996-09-09Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Chlorpromazine Tablets B.P. 25mgtablet25 mgoralClonmel Healthcare Limited1992-12-311996-09-09Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Chlorpromazine Tablets B.P. 50mgtablet50 mgoralClonmel Healthcare Limited1992-12-311996-09-09Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Largactil 100liquid100 mgoralSanofi Aventis Canada Inc1963-12-312006-07-28Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Largactil 25liquid25 mgoralSanofi Aventis Canada Inc1960-12-312006-07-28Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Largactil 50solution50 mgintramuscular; intravenousAventis Pharma Inc1952-12-312005-08-01Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Largactil Drops 40mg/mldrops40 mgoralSanofi Aventis Canada Inc1952-12-312007-01-30Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Largactil Sup 100mgsuppository100 mgrectalSanofi Aventis Canada Inc1952-12-312006-07-28Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Novo-chlorpromazine 200mgtablet223.2 mgoralNovopharm Limited1970-12-312005-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Novo-chlorpromazine Tab 10mgtablet11.16 mgoralNovopharm Limited1971-12-312005-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Teva-chlorpromazinetablet50.0 mgoralTeva Canada Limited1967-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Teva-chlorpromazinetablet100 mgoralTeva Canada Limited1967-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Teva-chlorpromazinetablet25.0 mgoralTeva Canada Limited1967-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Chlorpromazinetablet27.9 mgoralApotex Inc1976-12-312011-08-05Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Apo Chlorpromazinetablet111.4 mgoralApotex Inc1976-12-312011-08-05Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Apo Chlorpromazinetablet55.7 mgoralApotex Inc1976-12-312011-08-05Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Chlorpromazinetablet, film coated25 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1973-01-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazinetablet, film coated100 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1973-01-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazinetablet, film coated50 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1973-01-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, film coated25 mg/1oralPhysicians Total Care, Inc.1973-01-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated200 mg/1oralUpsher Smith Laboratories, Inc.2011-08-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated100 mg/1oralContract Pharmacy Services Pa2010-02-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated200 mg/1oralMylan Institutional Inc.1994-11-28Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochlorideinjection25 mg/mLintramuscularWest Ward Pharmaceutical Corp.1974-07-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated100 mg/1oralClinical Solutions Wholesale, Llc1974-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated50 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated25 mg/1oralUpsher Smith Laboratories, Inc.2011-08-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated25 mg/1oralTYA Pharmaceuticals1974-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated100 mg/1oralMylan Institutional Inc.1994-11-28Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochlorideinjection25 mg/mLintramuscularWest Ward Pharmaceutical Corp.1974-07-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated200 mg/1oralClinical Solutions Wholesale, Llc1974-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated25 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated10 mg/1oralUpsher Smith Laboratories, Inc.2011-08-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochlorideinjection25 mg/mLintramuscularTYA Pharmaceuticals1974-07-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated50 mg/1oralMylan Institutional Inc.1994-11-23Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated25 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1974-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated25 mg/1oralClinical Solutions Wholesale, Llc1974-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated25 mg/1oralREMEDYREPACK INC.2013-05-06Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated200 mg/1oralSandoz Inc1974-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated200 mg/1oralTYA Pharmaceuticals2011-08-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet200 mg/1oralREMEDYREPACK INC.2011-08-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated100 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1974-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated25 mg/1oralCardinal Health2011-04-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated100 mg/1oralREMEDYREPACK INC.2013-03-13Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated100 mg/1oralSandoz Inc1974-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated100 mg/1oralClinical Solutions Wholesale2011-08-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet50 mg/1oralREMEDYREPACK INC.2010-08-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated50 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs1974-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated50 mg/1oralCardinal Health2011-08-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated50 mg/1oralREMEDYREPACK INC.2013-02-21Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated50 mg/1oralSandoz Inc1974-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated200 mg/1oralClinical Solutions Wholesale2011-08-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated25 mg/1oralREMEDYREPACK INC.2010-12-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated25 mg/1oralCardinal Health2011-08-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated50 mg/1oralClinical Solutions Wholesale2011-08-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated25 mg/1oralMylan Institutional Inc.1994-11-23Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated25 mg/1oralSandoz Inc1974-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated200 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated100 mg/1oralUpsher Smith Laboratories, Inc.2011-08-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated50 mg/1oralContract Pharmacy Services Pa2010-02-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated100 mg/1oralCardinal Health2011-08-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated100 mg/1oralREMEDYREPACK INC.2010-12-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated10 mg/1oralMylan Institutional Inc.1994-11-23Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated10 mg/1oralSandoz Inc1974-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated25 mg/1oralClinical Solutions Wholesale2011-08-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated100 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated50 mg/1oralUpsher Smith Laboratories, Inc.2011-08-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Chlorpromazine Hydrochloridetablet, sugar coated100 mg/1oralTYA Pharmaceuticals1974-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
ChlorpromanylTechnilab (Canada)
LargactilSpecia
ThorazineGlaxoSmithKline
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Chlorpromazine hydrochloride
69-09-0
Thumb
  • InChI Key: FBSMERQALIEGJT-UHFFFAOYSA-N
  • Monoisotopic Mass: 354.072424754
  • Average Mass: 355.325
DBSALT000026
Categories
UNIIU42B7VYA4P
CAS number50-53-3
WeightAverage: 318.864
Monoisotopic: 318.095747015
Chemical FormulaC17H19ClN2S
InChI KeyInChIKey=ZPEIMTDSQAKGNT-UHFFFAOYSA-N
InChI
InChI=1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3
IUPAC Name
[3-(2-chloro-10H-phenothiazin-10-yl)propyl]dimethylamine
SMILES
CN(C)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Benzenoid
  • Aryl halide
  • Aryl chloride
  • Para-thiazine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Thioether
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of schizophrenia, control nausea and vomiting, For relief of restlessness and apprehension before surgery, adjunct in the treatment of tetanus, control the manifestations of the manic type of manic-depressive illness.
PharmacodynamicsChlorpromazine is a psychotropic agent indicated for the treatment of schizophrenia. It also exerts sedative and antiemetic activity. Chlorpromazine has actions at all levels of the central nervous system-primarily at subcortical levels-as well as on multiple organ systems. Chlorpromazine has strong antiadrenergic and weaker peripheral anticholinergic activity; ganglionic blocking action is relatively slight. It also possesses slight antihistaminic and antiserotonin activity.
Mechanism of actionChlorpromazine acts as an antagonist (blocking agent) on different postsysnaptic receptors -on dopaminergic-receptors (subtypes D1, D2, D3 and D4 - different antipsychotic properties on productive and unproductive symptoms), on serotonergic-receptors (5-HT1 and 5-HT2, with anxiolytic, antidepressive and antiaggressive properties as well as an attenuation of extrapypramidal side-effects, but also leading to weight gain, fall in blood pressure, sedation and ejaculation difficulties), on histaminergic-receptors (H1-receptors, sedation, antiemesis, vertigo, fall in blood pressure and weight gain), alpha1/alpha2-receptors (antisympathomimetic properties, lowering of blood pressure, reflex tachycardia, vertigo, sedation, hypersalivation and incontinence as well as sexual dysfunction, but may also attenuate pseudoparkinsonism - controversial) and finally on muscarinic (cholinergic) M1/M2-receptors (causing anticholinergic symptoms like dry mouth, blurred vision, obstipation, difficulty/inability to urinate, sinus tachycardia, ECG-changes and loss of memory, but the anticholinergic action may attenuate extrapyramidal side-effects). Additionally, Chlorpromazine is a weak presynaptic inhibitor of Dopamine reuptake, which may lead to (mild) antidepressive and antiparkinsonian effects. This action could also account for psychomotor agitation and amplification of psychosis (very rarely noted in clinical use).
AbsorptionReadily absorbed from the GI tract. Bioavailability varies due to first-pass metabolism by the liver.
Volume of distribution
  • 20 L/kg
Protein binding> 90% to plasma proteins, primarily albumin
Metabolism

Extensively metabolized in the liver and kidneys. It is extensively metabolized by cytochrome P450 isozymes CYP2D6 (major pathway), CYP1A2 and CYP3A4. Approximately 10 to 12 major metabolite have been identified. Hydroxylation at positions 3 and 7 of the phenothiazine nucleus and the N-dimethylaminopropyl side chain undergoes demethylation and is also metabolized to an N-oxide. In urine, 20% of chlopromazine and its metabolites are excreted unconjugated in the urine as unchanged drug, demonomethylchlorpromazine, dedimethylchlorpromazine, their sulfoxide metabolites, and chlorpromazine-N-oxide. The remaining 80% consists of conjugated metabolites, principally O-glucuronides and small amounts of ethereal sulfates of the mono- and dihydroxy-derivatives of chlorpromazine and their sulfoxide metabolites. The major metabolites are the monoglucuronide of N-dedimethylchlorpromazine and 7-hydroxychlorpromazine. Approximately 37% of the administered dose of chlorpromazine is excreted in urine.

SubstrateEnzymesProduct
Chlorpromazine
hydroxychlorpromazineDetails
Chlorpromazine
Not Available
chlorpromazine-N-oxideDetails
Chlorpromazine
Not Available
dedimethylchlorpromazineDetails
Chlorpromazine
Not Available
demonomethylchlorpromazineDetails
Chlorpromazine
Not Available
N-dedimethylchlorpromazineDetails
Route of eliminationKidneys, ~ 37% excreted in urine
Half life~ 30 hours
ClearanceNot Available
ToxicityAgitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, restlessness
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9757
Blood Brain Barrier+0.9795
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.787
P-glycoprotein inhibitor IInhibitor0.7164
P-glycoprotein inhibitor IIInhibitor0.8387
Renal organic cation transporterInhibitor0.7557
CYP450 2C9 substrateNon-substrate0.7617
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.6477
CYP450 1A2 substrateInhibitor0.9305
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.9422
CYP450 2C19 inhibitorInhibitor0.5512
CYP450 3A4 inhibitorNon-inhibitor0.9375
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6601
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9309
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.3196 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9536
hERG inhibition (predictor II)Inhibitor0.787
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
  • Actavis mid atlantic llc
  • Pharmaceutical assoc inc div beach products
  • Wockhardt eu operations (swiss) ag
  • Roxane laboratories inc
  • Sandoz inc
  • Abraxis pharmaceutical products
  • Baxter healthcare corp anesthesia and critical care
  • Marsam pharmaceuticals llc
  • Watson laboratories inc
  • Wyeth ayerst laboratories
  • Alpharma us pharmaceuticals division
  • Abbott laboratories pharmaceutical products div
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Kv pharmaceutical co
  • Lederle laboratories div american cyanamid co
  • Purepac pharmaceutical co
  • Private formulations inc
  • Usl pharma inc
  • Vangard laboratories inc div midway medical co
  • West ward pharmaceutical corp
  • Parke davis div warner lambert co
Packagers
Dosage forms
FormRouteStrength
Tabletoral111.4 mg
Tabletoral55.7 mg
Tabletoral111.6 mg
Tabletoral27.9 mg
Tabletoral55.8 mg
Dropsoral22.2 mg
Syruporal44.5 mg
Tablet, film coatedoral100 mg/1
Tablet, film coatedoral25 mg/1
Tablet, film coatedoral50 mg/1
Liquidintramuscular; intravenous25 mg
Solutionintramuscular; intravenous25 mg
Injectionintramuscular25 mg/mL
Tabletoral200 mg/1
Tabletoral50 mg/1
Tablet, sugar coatedoral10 mg/1
Tablet, sugar coatedoral100 mg/1
Tablet, sugar coatedoral200 mg/1
Tablet, sugar coatedoral25 mg/1
Tablet, sugar coatedoral50 mg/1
Liquidintramuscular; intravenous27.9 mg
Tabletoral25 mg
Tabletoral50 mg
Liquidoral100 mg
Liquidoral25 mg
Solutionintramuscular; intravenous50 mg
Dropsoral40 mg
Suppositoryrectal100 mg
Tabletoral223.2 mg
Tabletoral11.16 mg
Tabletoral100 mg
Tabletoral25.0 mg
Tabletoral50.0 mg
Prices
Unit descriptionCostUnit
Chlorpromazine 25 mg/ml amp8.04USD ml
ChlorproMAZINE HCl 200 mg tablet1.19USD tablet
Chlorpromazine 200 mg tablet1.05USD tablet
ChlorproMAZINE HCl 100 mg tablet0.84USD tablet
ChlorproMAZINE HCl 50 mg tablet0.73USD tablet
ChlorproMAZINE HCl 25 mg tablet0.55USD tablet
Chlorpromazine 100 mg tablet0.39USD tablet
ChlorproMAZINE HCl 10 mg tablet0.37USD tablet
Chlorpromazine 10 mg tablet0.32USD tablet
Chlorpromazine 50 mg tablet0.3USD tablet
Chlorpromazine 25 mg tablet0.17USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
melting point177-178Charpentier, P.; U S . Patent 2,645,640; July 14, 1953; assigned to Societe des Usines Chimiques Rhone-Poulenc, France
boiling point200-205 °C at 8.00E-01 mm HgPhysProp
water solubility2.55 mg/L (at 24 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP5.41AVDEEF,A (1995)
logS-5.01ADME Research, USCD
Caco2 permeability-4.7ADME Research, USCD
pKa9.3 (at 25 °C)HANSCH,C & LEO,AJ (1985)
Predicted Properties
PropertyValueSource
Water Solubility0.00417 mg/mLALOGPS
logP5.18ALOGPS
logP4.54ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)9.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.76 m3·mol-1ChemAxon
Polarizability35.1 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.36 KB)
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-z9c4000000-ed14fee152701eacf689View in MoNA
References
Synthesis Reference

Charpentier, P.; U S . Patent 2,645,640; July 14, 1953; assigned to Societe des Usines Chimiques Rhone-Poulenc, France.

US2645640
General References
  1. Leucht S, Wahlbeck K, Hamann J, Kissling W: New generation antipsychotics versus low-potency conventional antipsychotics: a systematic review and meta-analysis. Lancet. 2003 May 10;361(9369):1581-9. Pubmed
External Links
ATC CodesN05AA01
AHFS Codes
  • 28:16.08.24
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (75.4 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Chlorpromazine can be increased when it is combined with Abiraterone.
AclidiniumAclidinium may increase the anticholinergic activities of Chlorpromazine.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Chlorpromazine.
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Chlorpromazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
AmisulprideThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Amisulpride.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Chlorpromazine.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Chlorpromazine.
AmphetamineChlorpromazine may decrease the stimulatory activities of Amphetamine.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Chlorpromazine.
AzelastineChlorpromazine may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Chlorpromazine.
BenzphetamineChlorpromazine may decrease the stimulatory activities of Benzphetamine.
Botulinum Toxin Type AChlorpromazine may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BChlorpromazine may increase the anticholinergic activities of Botulinum Toxin Type B.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Chlorpromazine.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Chlorpromazine.
BromocriptineThe therapeutic efficacy of Chlorpromazine can be decreased when used in combination with Bromocriptine.
BuprenorphineChlorpromazine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Chlorpromazine.
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Chlorpromazine.
Calcium carbonateCalcium carbonate can cause a decrease in the absorption of Chlorpromazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
CathinoneChlorpromazine may decrease the stimulatory activities of Cathinone.
Cimetropium BromideChlorpromazine may increase the anticholinergic activities of Cimetropium Bromide.
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Chlorpromazine.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Chlorpromazine.
CobicistatThe serum concentration of Chlorpromazine can be increased when it is combined with Cobicistat.
CodeineThe therapeutic efficacy of Codeine can be decreased when used in combination with Chlorpromazine.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Chlorpromazine.
DarunavirThe serum concentration of Chlorpromazine can be increased when it is combined with Darunavir.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Chlorpromazine.
DesmopressinThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Desmopressin.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Chlorpromazine.
DextroamphetamineChlorpromazine may decrease the stimulatory activities of Dextroamphetamine.
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Chlorpromazine.
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Chlorpromazine.
DofetilideChlorpromazine may increase the QTc-prolonging activities of Dofetilide.
DonepezilDonepezil may increase the central neurotoxic activities of Chlorpromazine.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Chlorpromazine.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Chlorpromazine.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Chlorpromazine.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Chlorpromazine.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Chlorpromazine.
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Chlorpromazine.
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Chlorpromazine.
EluxadolineChlorpromazine may increase the activities of Eluxadoline.
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Ergoloid mesylate is combined with Chlorpromazine.
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Chlorpromazine.
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Chlorpromazine.
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Chlorpromazine.
EthanolChlorpromazine may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Chlorpromazine.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Chlorpromazine.
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Chlorpromazine.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Chlorpromazine.
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Chlorpromazine.
GalantamineGalantamine may increase the central neurotoxic activities of Chlorpromazine.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Glucagon recombinant.
GoserelinGoserelin may increase the QTc-prolonging activities of Chlorpromazine.
HaloperidolChlorpromazine may increase the QTc-prolonging activities of Haloperidol.
HydrocodoneChlorpromazine may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Chlorpromazine.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Chlorpromazine.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Chlorpromazine.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Chlorpromazine.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Chlorpromazine.
IvabradineIvabradine may increase the QTc-prolonging activities of Chlorpromazine.
LeuprolideLeuprolide may increase the QTc-prolonging activities of Chlorpromazine.
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Chlorpromazine.
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Chlorpromazine.
LisdexamfetamineChlorpromazine may decrease the stimulatory activities of Lisdexamfetamine.
LithiumLithium may increase the neurotoxic activities of Chlorpromazine.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Chlorpromazine.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Chlorpromazine.
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Chlorpromazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Chlorpromazine.
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Chlorpromazine.
MequitazineChlorpromazine may increase the arrhythmogenic activities of Mequitazine.
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Chlorpromazine.
MethamphetamineChlorpromazine may decrease the stimulatory activities of Methamphetamine.
MethotrimeprazineChlorpromazine may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.
MethylphenidateThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Methylphenidate.
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Chlorpromazine.
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Chlorpromazine.
MetyrosineChlorpromazine may increase the sedative activities of Metyrosine.
MianserinMianserin may increase the anticholinergic activities of Chlorpromazine.
MifepristoneMifepristone may increase the QTc-prolonging activities of Chlorpromazine.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Chlorpromazine.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Chlorpromazine.
MirabegronThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Mirabegron.
MirtazapineChlorpromazine may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Chlorpromazine.
MorphineChlorpromazine may increase the hypotensive activities of Morphine.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Chlorpromazine.
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Chlorpromazine.
NebivololThe serum concentration of Nebivolol can be increased when it is combined with Chlorpromazine.
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Chlorpromazine.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Chlorpromazine.
OctreotideOctreotide may increase the QTc-prolonging activities of Chlorpromazine.
OrphenadrineChlorpromazine may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
PanobinostatThe serum concentration of Chlorpromazine can be increased when it is combined with Panobinostat.
ParaldehydeChlorpromazine may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Paroxetine.
Peginterferon alfa-2bThe serum concentration of Chlorpromazine can be decreased when it is combined with Peginterferon alfa-2b.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Chlorpromazine.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Chlorpromazine.
PhendimetrazineChlorpromazine may decrease the stimulatory activities of Phendimetrazine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Chlorpromazine.
PhentermineChlorpromazine may decrease the stimulatory activities of Phentermine.
PorfimerChlorpromazine may increase the photosensitizing activities of Porfimer.
Potassium ChlorideChlorpromazine may increase the ulcerogenic activities of Potassium Chloride.
PramlintidePramlintide may increase the anticholinergic activities of Chlorpromazine.
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Chlorpromazine.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Chlorpromazine.
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Chlorpromazine.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Chlorpromazine.
PyrimethamineThe serum concentration of Chlorpromazine can be increased when it is combined with Pyrimethamine.
QuinagolideThe therapeutic efficacy of Quinagolide can be decreased when used in combination with Chlorpromazine.
RamosetronChlorpromazine may increase the activities of Ramosetron.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Chlorpromazine.
RitonavirThe metabolism of Chlorpromazine can be decreased when combined with Ritonavir.
RivastigmineRivastigmine may increase the central neurotoxic activities of Chlorpromazine.
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Chlorpromazine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Chlorpromazine.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Chlorpromazine.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Chlorpromazine.
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Chlorpromazine.
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Chlorpromazine.
SulpirideThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Sulpiride.
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Chlorpromazine.
SuvorexantChlorpromazine may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TacrineThe therapeutic efficacy of Chlorpromazine can be decreased when used in combination with Tacrine.
TamoxifenThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Chlorpromazine resulting in a loss in efficacy.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Chlorpromazine.
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tedizolid Phosphate is combined with Chlorpromazine.
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Chlorpromazine.
ThalidomideChlorpromazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ThiopentalThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Thiopental.
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Chlorpromazine.
TiclopidineThe metabolism of Chlorpromazine can be decreased when combined with Ticlopidine.
TiotropiumChlorpromazine may increase the anticholinergic activities of Tiotropium.
TopiramateThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Topiramate.
TramadolThe therapeutic efficacy of Tramadol can be decreased when used in combination with Chlorpromazine.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Chlorpromazine.
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Chlorpromazine.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Chlorpromazine.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Chlorpromazine.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Chlorpromazine.
Valproic AcidThe serum concentration of Valproic Acid can be increased when it is combined with Chlorpromazine.
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Chlorpromazine.
VerteporfinChlorpromazine may increase the photosensitizing activities of Verteporfin.
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Chlorpromazine.
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Chlorpromazine.
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Chlorpromazine.
ZolpidemChlorpromazine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation.

Targets

1. D(2) dopamine receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
D(2) dopamine receptor P14416 Details

References:

  1. Oades RD, Rao ML, Bender S, Sartory G, Muller BW: Neuropsychological and conditioned blocking performance in patients with schizophrenia: assessment of the contribution of neuroleptic dose, serum levels and dopamine D2-receptor occupancy. Behav Pharmacol. 2000 Jun;11(3-4):317-30. Pubmed
  2. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. Pubmed
  3. Wu S, Xing Q, Gao R, Li X, Gu N, Feng G, He L: Response to chlorpromazine treatment may be associated with polymorphisms of the DRD2 gene in Chinese schizophrenic patients. Neurosci Lett. 2005 Mar 7;376(1):1-4. Epub 2004 Dec 2. Pubmed
  4. Wu SN, Gao R, Xing QH, Li HF, Shen YF, Gu NF, Feng GY, He L: Association of DRD2 polymorphisms and chlorpromazine-induced extrapyramidal syndrome in Chinese schizophrenic patients. Acta Pharmacol Sin. 2006 Aug;27(8):966-70. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  6. Seeman P: Dopamine D2 receptors as treatment targets in schizophrenia. Clin Schizophr Relat Psychoses. 2010 Apr;4(1):56-73. Pubmed
  7. Roth BL, Craigo SC, Choudhary MS, Uluer A, Monsma FJ Jr, Shen Y, Meltzer HY, Sibley DR: Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors. J Pharmacol Exp Ther. 1994 Mar;268(3):1403-10. Pubmed
  8. Roth BL, Tandra S, Burgess LH, Sibley DR, Meltzer HY: D4 dopamine receptor binding affinity does not distinguish between typical and atypical antipsychotic drugs. Psychopharmacology (Berl). 1995 Aug;120(3):365-8. Pubmed

2. D(1A) dopamine receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
D(1A) dopamine receptor P21728 Details

References:

  1. Kanba S, Suzuki E, Nomura S, Nakaki T, Yagi G, Asai M, Richelson E: Affinity of neuroleptics for D1 receptor of human brain striatum. J Psychiatry Neurosci. 1994 Jul;19(4):265-9. Pubmed

3. 5-hydroxytryptamine receptor 2A

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2A P28223 Details

References:

  1. Kusumi I, Takahashi Y, Suzuki K, Kameda K, Koyama T: Differential effects of subchronic treatments with atypical antipsychotic drugs on dopamine D2 and serotonin 5-HT2A receptors in the rat brain. J Neural Transm. 2000;107(3):295-302. Pubmed
  2. Yamada J, Sugimoto Y, Horisaka K: Serotonin2 (5-HT2) receptor agonist 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) inhibits chlorpromazine- and haloperidol-induced hypothermia in mice. Biol Pharm Bull. 1995 Nov;18(11):1580-3. Pubmed

4. 5-hydroxytryptamine receptor 1A

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 1A P08908 Details

References:

  1. Cosi C, Koek W: Agonist, antagonist, and inverse agonist properties of antipsychotics at human recombinant 5-HT receptors expressed in HeLa cells. Eur J Pharmacol. 2001 Dec 14;433(1):55-62. Pubmed
  2. Newman-Tancredi A, Gavaudan S, Conte C, Chaput C, Touzard M, Verriele L, Audinot V, Millan MJ: Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study. Eur J Pharmacol. 1998 Aug 21;355(2-3):245-56. Pubmed

5. Alpha-1A adrenergic receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

References:

  1. Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. Pubmed

6. Alpha-1B adrenergic receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Alpha-1B adrenergic receptor P35368 Details

References:

  1. Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. Pubmed

7. Histamine H1 receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

References:

  1. Hals PA, Hall H, Dahl SG: Muscarinic cholinergic and histamine H1 receptor binding of phenothiazine drug metabolites. Life Sci. 1988;43(5):405-12. Pubmed
  2. Church MK, Young KD: The characteristics of inhibition of histamine release from human lung fragments by sodium cromoglycate, salbutamol and chlorpromazine. Br J Pharmacol. 1983 Apr;78(4):671-9. Pubmed
  3. Johnson HG, Miller MD: Inhibition of histamine release and ionophore-induced calcium flux in rat mast cells by lidocaine and chlorpromazine. Agents Actions. 1979 Aug;9(3):239-43. Pubmed
  4. Palmer GC, Wagner HR, Palmer SJ, Manian AA: Histamine-, norepinephrine-, and dopamine-sensitive central adenylate cyclases: effects of chlorpromazine derivatives and butaclamol. Arch Int Pharmacodyn Ther. 1978 Jun;233(2):314-25. Pubmed
  5. Ruffolo RR, Patil PN: Kinetics of blockade of different receptors by chlorpromazine in rabbit stomach strips. Eur J Pharmacol. 1978 Mar 15;48(2):151-7. Pubmed

8. Potassium voltage-gated channel subfamily H member 2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Potassium voltage-gated channel subfamily H member 2 Q12809 Details

References:

  1. Thomas D, Wu K, Kathofer S, Katus HA, Schoels W, Kiehn J, Karle CA: The antipsychotic drug chlorpromazine inhibits HERG potassium channels. Br J Pharmacol. 2003 Jun;139(3):567-74. Pubmed

9. D(1) dopamine receptor

Kind: Protein group

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
D(1A) dopamine receptor P21728 Details
D(1B) dopamine receptor P21918 Details

References:

  1. Seeman P, Van Tol HH: Dopamine receptor pharmacology. Curr Opin Neurol Neurosurg. 1993 Aug;6(4):602-8. Pubmed

10. D(3) dopamine receptor

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
D(3) dopamine receptor P35462 Details

References:

  1. Freedman SB, Patel S, Marwood R, Emms F, Seabrook GR, Knowles MR, McAllister G: Expression and pharmacological characterization of the human D3 dopamine receptor. J Pharmacol Exp Ther. 1994 Jan;268(1):417-26. Pubmed

11. D(4) dopamine receptor

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
D(4) dopamine receptor P21917 Details

References:

  1. Roth BL, Tandra S, Burgess LH, Sibley DR, Meltzer HY: D4 dopamine receptor binding affinity does not distinguish between typical and atypical antipsychotic drugs. Psychopharmacology (Berl). 1995 Aug;120(3):365-8. Pubmed

12. D(1B) dopamine receptor

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
D(1B) dopamine receptor P21918 Details

References:

  1. Seeman P, Van Tol HH: Dopamine receptor pharmacology. Curr Opin Neurol Neurosurg. 1993 Aug;6(4):602-8. Pubmed

13. 5-hydroxytryptamine receptor 2C

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2C P28335 Details

References:

  1. Roth BL, Craigo SC, Choudhary MS, Uluer A, Monsma FJ Jr, Shen Y, Meltzer HY, Sibley DR: Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors. J Pharmacol Exp Ther. 1994 Mar;268(3):1403-10. Pubmed

14. 5-hydroxytryptamine 2 receptor

Kind: Protein group

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2A P28223 Details
5-hydroxytryptamine receptor 2B P41595 Details
5-hydroxytryptamine receptor 2C P28335 Details

References:

  1. Roth BL, Craigo SC, Choudhary MS, Uluer A, Monsma FJ Jr, Shen Y, Meltzer HY, Sibley DR: Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors. J Pharmacol Exp Ther. 1994 Mar;268(3):1403-10. Pubmed

15. Alpha-1 adrenergic receptor

Kind: Protein group

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details
Alpha-1B adrenergic receptor P35368 Details
Alpha-1D adrenergic receptor P25100 Details

References:

  1. Huerta-Bahena J, Villalobos-Molina R, Garcia-Sainz JA: Trifluoperazine and chlorpromazine antagonize alpha 1- but not alpha2- adrenergic effects. Mol Pharmacol. 1983 Jan;23(1):67-70. Pubmed

16. Alpha-2 adrenergic receptor

Kind: Protein group

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Alpha-2A adrenergic receptor P08913 Details
Alpha-2B adrenergic receptor P18089 Details
Alpha-2C adrenergic receptor P18825 Details

References:

  1. Bylund DB, Ray-Prenger C, Murphy TJ: Alpha-2A and alpha-2B adrenergic receptor subtypes: antagonist binding in tissues and cell lines containing only one subtype. J Pharmacol Exp Ther. 1988 May;245(2):600-7. Pubmed

17. Muscarinic acetylcholine receptor M1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

References:

  1. Davies MA, Compton-Toth BA, Hufeisen SJ, Meltzer HY, Roth BL: The highly efficacious actions of N-desmethylclozapine at muscarinic receptors are unique and not a common property of either typical or atypical antipsychotic drugs: is M1 agonism a pre-requisite for mimicking clozapine’s actions? Psychopharmacology (Berl). 2005 Apr;178(4):451-60. Epub 2004 Oct 13. Pubmed

18. Muscarinic acetylcholine receptor M3

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M3 P20309 Details

References:

  1. Davies MA, Compton-Toth BA, Hufeisen SJ, Meltzer HY, Roth BL: The highly efficacious actions of N-desmethylclozapine at muscarinic receptors are unique and not a common property of either typical or atypical antipsychotic drugs: is M1 agonism a pre-requisite for mimicking clozapine’s actions? Psychopharmacology (Berl). 2005 Apr;178(4):451-60. Epub 2004 Oct 13. Pubmed

19. Sphingomyelin phosphodiesterase

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Sphingomyelin phosphodiesterase P17405 Details

References:

  1. Yoshida Y, Arimoto K, Sato M, Sakuragawa N, Arima M, Satoyoshi E: Reduction of acid sphingomyelinase activity in human fibroblasts induced by AY-9944 and other cationic amphiphilic drugs. J Biochem. 1985 Dec;98(6):1669-79. Pubmed

20. Calmodulin

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Calmodulin P62158 Details

References:

  1. Marshak DR, Lukas TJ, Watterson DM: Drug-protein interactions: binding of chlorpromazine to calmodulin, calmodulin fragments, and related calcium binding proteins. Biochemistry. 1985 Jan 1;24(1):144-50. Pubmed

21. alpha1-acid glycoprotein

Kind: Protein group

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Alpha-1-acid glycoprotein 1 P02763 Details
Alpha-1-acid glycoprotein 2 P19652 Details

References:

  1. Herve F, Duche JC, d’Athis P, Marche C, Barre J, Tillement JP: Binding of disopyramide, methadone, dipyridamole, chlorpromazine, lignocaine and progesterone to the two main genetic variants of human alpha 1-acid glycoprotein: evidence for drug-binding differences between the variants and for the presence of two separate drug-binding sites on alpha 1-acid glycoprotein. Pharmacogenetics. 1996 Oct;6(5):403-15. Pubmed

22. 5-hydroxytryptamine receptor 6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 6 P50406 Details

References:

  1. Roth BL, Craigo SC, Choudhary MS, Uluer A, Monsma FJ Jr, Shen Y, Meltzer HY, Sibley DR: Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors. J Pharmacol Exp Ther. 1994 Mar;268(3):1403-10. Pubmed

23. 5-hydroxytryptamine receptor 7

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 7 P34969 Details

References:

  1. Roth BL, Craigo SC, Choudhary MS, Uluer A, Monsma FJ Jr, Shen Y, Meltzer HY, Sibley DR: Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors. J Pharmacol Exp Ther. 1994 Mar;268(3):1403-10. Pubmed

24. Histamine H4 receptor

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Histamine H4 receptor Q9H3N8 Details

References:

  1. Nguyen T, Shapiro DA, George SR, Setola V, Lee DK, Cheng R, Rauser L, Lee SP, Lynch KR, Roth BL, O’Dowd BF: Discovery of a novel member of the histamine receptor family. Mol Pharmacol. 2001 Mar;59(3):427-33. Pubmed

Enzymes

1. Cytochrome P450 2D6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression] Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. Pubmed
  2. Otani K, Aoshima T: Pharmacogenetics of classical and new antipsychotic drugs. Ther Drug Monit. 2000 Feb;22(1):118-21. Pubmed
  3. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  4. Yoshii K, Kobayashi K, Tsumuji M, Tani M, Shimada N, Chiba K: Identification of human cytochrome P450 isoforms involved in the 7-hydroxylation of chlorpromazine by human liver microsomes. Life Sci. 2000;67(2):175-84. Pubmed
  5. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. Pubmed
  6. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Yoshii K, Kobayashi K, Tsumuji M, Tani M, Shimada N, Chiba K: Identification of human cytochrome P450 isoforms involved in the 7-hydroxylation of chlorpromazine by human liver microsomes. Life Sci. 2000;67(2):175-84. Pubmed
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. Pubmed
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 3A4

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 2E1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

References:

  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cholinesterase

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cholinesterase P06276 Details

References:

  1. Nasello AG, Gidali D, Felicio LF: A comparative study of the anticholinesterase activity of several antipsychotic agents. Pharmacol Biochem Behav. 2003 Jul;75(4):895-901. Pubmed
  2. Muraoka S, Miura T: Inactivation of cholinesterase induced by chlorpromazine cation radicals. Pharmacol Toxicol. 2003 Feb;92(2):100-4. Pubmed
  3. Spinedi A, Pacini L, Limatola C, Luly P, Farias RN: A study of human erythrocyte acetylcholinesterase inhibition by chlorpromazine. Biochem J. 1991 Sep 1;278 ( Pt 2):461-3. Pubmed

Carriers

1. Serum albumin

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Kitamura K, Omran AA, Nagata C, Kamijima Y, Tanaka R, Takegami S, Kitade T: Effects of inorganic ions on the binding of triflupromazine and chlorpromazine to bovine serum albumin studied by spectrometric methods. Chem Pharm Bull (Tokyo). 2006 Jul;54(7):972-6. Pubmed
  2. Rukhadze MD, Bezarashvili GS, Sidamonidze NS, Tsagareli SK: Investigation of binding process of chlorpromazine to bovine serum albumin by means of passive and active experiments. Biomed Chromatogr. 2001 Oct;15(6):365-73. Pubmed
  3. Silva D, Cortez CM, Louro SR: Quenching of the intrinsic fluorescence of bovine serum albumin by chlorpromazine and hemin. Braz J Med Biol Res. 2004 Jul;37(7):963-8. Epub 2004 Jun 22. Pubmed

Transporters

1. Multidrug resistance protein 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. Pubmed
  2. Boulton DW, DeVane CL, Liston HL, Markowitz JS: In vitro P-glycoprotein affinity for atypical and conventional antipsychotics. Life Sci. 2002 May 31;71(2):163-9. Pubmed

2. Solute carrier family 22 member 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 1 O15245 Details

References:

  1. Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. Pubmed

3. Bile salt export pump

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Bile salt export pump O95342 Details

References:

  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on April 04, 2014 11:41